


Winchestered

by hannahindie



Category: Supernatural
Genre: Dean Winchester - Freeform, F/M, Humor, Reader Insert, Scrooged, Supernatural - Freeform, ghost of christmas future - Freeform, ghost of christmas past - Freeform, slight angst, spn fanfic, supernatural fanfiction - Freeform
Language: English
Status: Completed
Published: 2018-12-12
Updated: 2018-12-12
Packaged: 2019-09-17 03:26:18
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,896
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16966794
Author URL: https://archiveofourown.org/users/hannahindie/pseuds/hannahindie
Summary: Dean gets a little visit from some less than savory characters to remind him that no matter what, life finds a way of doing what it wants regardless of how much you try to change it.





	Winchestered

_Motherfucker._

I groaned, my head aching as I turned on the hard surface I was laying on and squinted at the old man across from me who was singing obnoxiously loud.

_Hi di-diddly-idle-um, diddly-doodle-idle-um, diddly-doo-ri-diddlum-deh  
Hi di-diddly-idle-um, diddly-doodle-idle-um, diddly-doo-ri-diddlum-deh_

He gave me a nearly toothless grin and I groaned again as I squeezed my eyes shut.

“What the hell are you singing, and why?”

“It’s Christmas time, m’boy. Will pro’ly be m’last one, and it’s m’ favorite tune. Thought I’d serenade ya good and proper.”

“That…that isn’t a Christmas song.” I rolled back over and tried to ignore him, my head pounding. I don’t know what the fuck I did or where I was last night, but being in the drunk tank of some podunk town was not exactly where I wanted to be - especially on Christmas. Sammy was gonna kill me.

“Oh, but fer ya, ‘tis. Ya don’t recognize where ya are, do ya?”

“I’m in some town in BFE, when I should be…well, anywhere else. I’m guessing I tied one on a little harder than I planned. And now here I am, trying to ignore some old man trying and failing to sing an Irish ballad and wondering where my brother is so he can get me the fuck outta here. Does that sound about right?”

“Well, son, ya ain’t wrong. But that ain’t what I was talkin’ about.” He slid over closer to me and I rolled back over to look at him.

“What the hell _are_ you talking about?”

“Why don’t ya sit up and take a good look, see where ya are, and then mebbe I’ll tell ya.”

I groaned and sat up, if for no other reason than to shut him up, and I leaned my head in my hands. _Jesus, what did I do?_ “Okay, I’m up. What am I looking at?”

“Just _look_.” 

I sighed and looked up, the light searing into my hungover eye sockets like lasers. The room was oddly familiar, and I ground the heel of my hand into my eyes. “This…where am I?”

The old man chuckled and I glared at him. He cleared his throat as he stood and walked over to the wall of steel bars that had us trapped. “Ain’t so much as _where_ , lad, but _when_.” He motioned for me to join him and I stood up with a groan, then stumbled to the bars and looked out. Suddenly, it hit me where I was.

“How…this…but I wasn’t even _here_ , Sam and I are somewhere in Mississippi,” I mumbled more to myself than the crazy old man who was grinning at me like he’d won the lottery. Judging by my surroundings, I wasn’t in Mississippi…I was in New York, although the drunk tank still made sense. But if that was the case… “This happened…hell…twenty years ago. Unless you’re an angel, I know I didn’t time travel. What the hell is this?”

“Did ya have a favorite Christmas movie, m’boy?”

I glared, “What does that have to do with anything?”

“Well, did ya?” He cocked an eyebrow at me and I had the overwhelming urge to punch him in the face.

“Well, I know this isn’t Die Hard…aw, shit, you’ve got to be kidding me. Scrooged? _Seriously?_ Nah, this is…I got hit really hard in the head, didn’t I? That’s what this is, because it can’t be because I’m some selfish bastard that never does anything for anybody.” I turned to look at the old man, “Because that’s _bullshit_. I might hate myself, but even I can recognize that I have given up _everything_ for this godforsaken hell hole of a planet.”

“It ain’t always about bein’ selfish, laddie. Sometimes it’s just about showin’ ya what you already know.”

I rolled my eyes, “What the hell is that supposed to mean?” He nodded his head towards the bars and I looked out to see the last person I expected to be there. “Y/N?”

She stopped short of the bars and crossed her arms, “You know, it doesn’t look great for an FBI agent to be tossed into the drunk tank, much less on Christmas Eve. What were you thinking, Winchester?”

“Y/N, I-” I stopped short when I heard someone respond…when I heard _myself_ respond, rather snarkily.

“Aww, c’mon, sweetheart. I was just celebrating, _alone_ I might add, because _someone_ didn’t want to come with me. We finished the job in record time, we did it well, and we don’t have anything lined up for the next few days.” I turned around to see myself stand up from the bed, then walk over and lean haphazardly against the bars. “Bust me outta here and let’s go have some fun, huh?”

I rolled my eyes, “I don’t act like that, that’s not remotely accurate.”

“‘Tis a memory, lad. Sorry to say it, but m’thinks tha’ twenty years ago, you pro’lly did act like that. Just keep watchin’.”

Y/N motioned to the guard, who came over and unlocked the cell door. Younger me strolled out, gave the guard a wink, then followed Y/N down the hall and out of the jail. I followed close behind, the old man trailing after me. “You’re lucky I was with you. You realize John would have just left you in there.”

“Yea, yea, I know. But you’re not my old man, and for once it’s just us. No Dad, no Sammy…just us.” He stopped Y/N as I looked on, my heart aching at how beautiful she was in the bright light of the moon. “We’re in New York, why don’t we make the best of it, huh?”

“And do what, Dean? It’s freezing cold, you hate museums and musicals-”

“Hey, I don’t hate ‘em! I’m just very particular about them.” He grabbed Y/N’s hands and rubbed them between his, “What about I take you to Broadway, we’ll go to one of those musicals you’re always going on about? Maybe we can go to Rockefeller Center, go ice skating.”

She laughed and I smiled; God, I missed that laugh. I missed the sound of it, and how her nose crinkled and her eyes squeezed shut. I missed the way she’d laugh so hard she would snort, which would throw her into another round of laughter that caused tears and hiccups as she tried to calm down. I missed _her_.

“Okay, fine. But you’re paying since I had to bail you out.” He laughed and held his arm out to her.

“Fair enough.” They walked away together in the darkness and I sighed.

“What’s the point in this, old man? Just to remind me of what? That I lost my best friend? That everything that happened from here on out was a catastrophic failure? Because I knew that already. I’ve known it for awhile.”

He gave me a sad smile and shook his head, “Let’s go. We’ve got a coupla more stops to make, don’t wanna lose track o’ time.” He reached out to me and I took a step back.

“I don’t think so. I’m done with this. I’ll wake up, and I’ll be in the floor of some abandoned house, and I’ll have to hear from Sammy how I got my ass handed to me. I’m over it, man.” I turned to walk away and suddenly a hand gripped my upper arm tightly. 

“We ain’t done until I say it’s done, m’boy,” the old man practically growled,”Ya need to understand it’s not always about ya, or what ya want. Now, c’mon.” That’s about the time everything went black. 

* * *

When I woke up, I was sitting on a bench directly on Broadway, and although I got a couple of weird looks, people walked around my legs like nothing was wrong. I guess I wasn’t the first person to jut my legs out into the middle of the sidewalk. “What the hell…”

“Ya say that an awful lot, don’t ya?” I looked up to see the man from before and groaned.

“Well, that tends to be the reaction of someone who keeps getting zapped through time.” I sat up and stretched, “What’s your name anyway?”

“My rightful title is the Ghost of Christmas Past, but ya can call me Neal.”

I raised an eyebrow, “Neal? Really?”

He shrugged, “Ya can call me by m’full name, but that is a bit much, ain’t it? Neal is fine.”

I stood up and shoved my hands in my pockets, “Okay _Neal_ , why are we here?”

He gestured toward the building in front of me and I looked up to see a sign advertising _Annie Get Your Gun_. The doors flew open and a crowd of people poured out, young me and Y/N trailing after the group, laughing and smiling. Y/N jabbed young me in the ribs with her elbow.

“Admit it, you loved it.”

He shrugged, “It was okay. Annie Oakley is pretty cool, so I admit…for a musical…it was pretty good. But don’t expect me to admit that to anyone else, I’ll deny it.” He grabbed Y/n by the waist and she smiled.

“What do you think you’re doing, Dean Winchester?”

He grinned and winked, “Something I should have done a long time ago.” He bent down and kissed her, and I couldn’t help but smile at the memory. I watched as the crowd swarmed around them, how oblivious they were to the swirling bodies that bumped against them as they exited the theater. He pulled back and she looked up at him, her eyes wide. I remember when she used to look at me like that; it was like I was the only person that existed.

“Why are you looking at me like that?” she asked, her voice low.

He smiled as he brushed hair from her face, and it took everything I had not to reach out and try to do the same myself, “You’re beautiful, do you realize that? The prettiest girl in all of New York.”

She blushed, “Oh _shut up_. Quit trying to impress me, even though it _might_ be working.” He grinned and grabbed her hand.

“Let’s go.” The two took off down the sidewalk and Neal and I followed. They stopped at the corner, and from down the street, the smooth voice of Frank Sinatra carried all the way to where they were standing. He leaned down and kissed her again, and this time, she kissed back. I closed my eyes as I remembered the spark, how my hands had sunk into her hair, how she had clung to me as if she was afraid to let go. By the time I opened my eyes, they were gone, drawn into the crowd as they made their way to the next destination.

“Aren’t we going to follow them? I mean…us?”

Neal shrugged, “Do ya remember what happens next?”

I nodded, “I took her to Rockefeller Center to ice skate. It was crowded as hell, not exactly as romantic as I had pictured it, but she loved every second of it. I busted my ass more than once, but she was flawless. Kind of reminded me of when she hunted, graceful but still dangerous…like she knew something everyone else didn’t. She…we…were happy.” I sighed and turned to face Neal again, “Why are we doing this? What is the point in all this?”

Neal smiled and gave a small shrug, “Now if I told ya that, laddie, it would defeat the purpose. Go on, now. It’s time to move on.”

“What do you mean? Isn’t there a schedule to this, like the next one comes at midnight tomorrow to collect me and show me the error of my ways? I mean, that’s what-”

Before I could finish my sentence, Neal was gone and I wasn’t in New York anymore. I was standing outside an abandoned house, alone.

* * *

I looked around, the setting familiar but not, and threw my hands up. “Seriously, Neal? No warning, no recoup time, just straight into the next one?”

“We don’t really have time for that, it’s not like we’re filming a movie.”

I jumped at the sudden voice and turned to face the source. A short woman with messy blonde hair was standing behind me, her hands jammed in her pockets and a look of semi-annoyance on her face. “Oh, great, so I guess you’re the fairy that smacks me around. Just what I needed.”

She shrugged, “I don’t have to smack you around, unless you’re into that kind of thing. Not a fairy either. Name’s Alice, but you can call me Al.”

“Well, it’s not nice to meet you, Al.” I turn and look back at the house, “What is this place?”

“I don’t know, this is your life, dude. I just show you want you need to see.” Before I can say anything else, I hear a snap and Al and I are standing in the dilapidated living room. Sammy is leaned against a doorway, his arms crossed as he watched Y/N flip through a giant book.

“Wait…this is…this is house we’re holed up in in Mississippi. What’s Y/N doing there? It was just me and Sam on this job…” Al shrugged again and I rolled my eyes, “Is that all you do, just shrug?”

“Yea, mostly.”

“Sam, stop it. It’s not going to work.” I look at Y/N, who had spoken without looking up.

“What are you talking about? I legitimately needed help, and since Dean is MIA, I thought maybe you could be useful.” Sam was lying, I could see it on his face. If I knew Y/N well enough, she also knew.

“Bullshit. He made his choice, quit trying to Parent Trap us. Where is he anyway? Out with his latest Christmas Eve conquest?”

She said it with a laugh, but I could see the look on her face, and it broke my heart. “Y/N, I swear, I’m not with anyone! I don’t…I don’t know what’s happening, but…it’s not that.”

“She can’t hear you, you know.”

“I know she can’t fucking hear me, Al! Dammit, what is this supposed to teach me, huh? That I shouldn’t have broken up with her? That I should have drug her into a life of pain and uncertainty, and having to watch me die over and over because this life sure as hell won’t let me go. Is that it? Because I won’t do that. I _can’t_ do that. Not to her.”

“Looks like she’s still doing it, even without you.”

I glared at her, “It’s not been that long. She’ll get out eventually. She wasn’t born into this life, and she doesn’t have to stay in it. I should kick Sam’s ass for even calling her.” I watched as Y/N slammed the book shut and grabbed her jacket.

“Come on, Sasquatch. I think I know what you’re dealing with, although I have a suspicion you already knew. Let’s get it over with so I can get out of here before Dean gets back.” Sam frowned but followed after her and I looked back at Al.

“Now what? Do we follow them?”

She shook her head, “Nah, we’re movin’ on. Like I said, we don’t have much time. We gotta jump ahead a little bit. You said something about Y/N moving on, yea?”

“Yea, but what does that-” I was interrupted by once again being zapped somewhere else, and I had a feeling I wasn’t going to like what we were about to see.

* * *

I was standing in the middle of a parking lot,  facing the front of a run down hotel, the sign flickering off and on in the darkness. It was raining, although it didn’t seem like I was actually getting wet. Al had flipped her hood up anyway and had lit a cigarette. I narrowed my eyes at her, “Are you fucking kidding me right now?” She shrugged and it took everything I had not to punch her. “Shrug one more time, Al. _One more time_ ,” I growled, my hands clenched at my sides.

She took a drag from her cigarette and gave me a tight lipped smile, “Sorry.” She nodded towards the building, “Don’t you want to see why we’re here?”

“Not really, but I guess you’re going to make me, right? So let’s get this shit over with.” I motioned in front of me, “After you, since you know where I’m supposed to be going.” Al walked past me and stopped at Room Thirteen.

“Your turn, Romeo.” I rolled my eyes and moved to open the door, but instead fell through it. The room was dark, but there was enough light coming from outside that I saw two body shaped lumps under the sheets. I watched as the one closest to the door slowly sat up and stretched. _Y/N_.  

“So you brought me here to show me she’s sleeping with someone else?”

“Quit bitching and keep watching.”

Y/N slipped from bed quietly and began gathering her clothes, but not before I got an eyeful of scars that hadn’t been there before. After she dressed, she sat down and pulled on her boots, carefully lacing them up, then grabbed her jacket and phone from the table. She walked towards the door, paused, went back to the night stand and dug through the wallet that was lying there and pocketed the cash she found. She gave one last look at the form still in bed, then carefully opened the door and shut it quietly behind her. Al and I walked through it, and watched as she hopped into her car and took off, throwing gravel out behind her as she sped off.

“She’s still hunting. And who was that bozo?”

“Who knows? Another hunter, some sorry jackass from the bar who was too drunk to notice all her scars? Does it really matter?”

“Of course it matters! She deserves….God, she deserves so much more than this.” I paused before I asked my next question; I wasn’t sure i wanted the answer. “Where…where am I?”

Al took another puff from her cigarette, then flicked it across the pavement, “I could show you, but there’s not much point. Let’s just say you end up where you started, only this time you don’t leave the cell.”

“What about Sam?” Sam would never leave me in there, not on my own.

“I don’t know. I’m only showing you what I was shown. Maybe Sam begrudgingly agrees to get your drunken ass out, or maybe he leaves you there because he’s tired of your bullshit. Knowing him, though, and your weird codependency, he’ll get you out. That’s not really the point here, Dean. Although I’m not surprised that’s where your brain went.”

I looked in the direction that Y/N had driven, “No, I know that wasn’t the point. She keeps hunting, and she doesn’t settle down. Her life doesn’t change just because I left her. That’s the point, right? That it doesn’t matter what any of us do, we’re all destined to do this anyway.”

“Basically.”

“You know, someone could have just told me that instead of going on this cliche little journey through time.”

Al pulled a cell phone from her pocket and ran her thumb down the screen ,”Yea, but would you have listened? I’m pretty sure time and experience have taught you otherwise.” She looked back up, “Sorry to cut this short, but I’ve got another appointment. So you understand, right? You get why we did this? Get your shit together, Winchester. Neal and I have better things to do than to keep trying to fix your fuck ups, alright? Go get the girl, already.” She snapped her fingers, and everything went black one more time.

* * *

I woke up in the Impala, sprawled out in the front seat. I sat up with a gasp and looked around, and realized that I was sitting outside out of a hotel rather than the house Sam and I had been in. “What the hell…” I mumbled, unsure of how I made it to the hotel, never mind with the car. I patted myself down, and not finding any injuries, I slowly climbed out and shut the door. I looked up and realized where I was.

_Room Thirteen._

It was definitely a different hotel, but the number was the same. Although it occurred to me that it might be a bad idea to just assume, I walked up to the door anyway and raised my hand to knock. The door swung open and the person on the other side gasped.

“Hey, Y/N,” I nearly whispered, afraid if I was any louder, she’d run. She looked up at me with wide eyes and I wondered if her heart was beating as fast as mine.

“Hi,” she answered just as quietly.

“I…I’m sorry, Y/N. I’m so sorry…I just…I wanted to protect you. But you’re just going to end up still hunting while I’m locked up in some drunk tank, and I don’t want you to rob the dudes you sleep with, it’s just not what I wanted for you at all-”

“Excuse me? Who am I robbing? Who said I’m sleeping with anybody-”

“Just listen, okay? Me pushing you away is not going to protect you. It doesn’t automatically mean you’re going to leave this life and go back to what you had before. The moment you found out about all this stuff, there wasn’t any chance of leaving it. I just…I didn’t want to be the reason you felt trapped, okay? I don’t want to be the reason your dreams are gone.”

Y/N smiled at me, a _genuine_ smile…one I haven’t seen in a long time. She put a hand against my cheek and tilted her head, “You’re a dumbass, Dean Winchester. _You’re_ the reason I’m still here to even have dreams. You didn’t take my old life away, you gave me a new one.” She kissed me, and it was like the world stopped. I closed my eyes and let her warmth sink in, deep into my bones. She pulled back and she laughed as I frowned at the separation. I opened my eyes to see her staring at me, “Wherever _you_ are…that’s where my dreams are, okay?”

“You don’t know how great it is to hear that, kid.” I paused, and she raised an eyebrow.

“What?”

“How’d you know I was out here, anyway? You opened the door before I even knocked.”

She shook her head, “No idea. I thought I heard your car and when I looked nothing was there. A couple of minutes later, something made me open the door and check again…and there you were. It was the strangest thing.” She stepped back through the doorway, “Would you like to come inside?”

I nodded and gave her a grin, “Absolutely.” I stopped as I stepped over the threshold and looked over my shoulder. In the distance Neal and Al were standing next to each other, Neal swaying drunkenly and Al smoking. Neal waved, then elbowed Al, who gave a half-hearted nod, and I nodded back. They slowly disappeared into the darkness and I smiled. _Merry Christmas, indeed._


End file.
